6-Cyclohexenyl-pyridine-2-carboxylic acid → 6-Cyclohexyl-pyridine-2-carboxylic acid

HRID 927343Notes

Reaction equation

HRID 927343 reaction equation
[C:1]1([C:7]2[N:12]=[C:11]([C:13]([OH:15])=[O:14])[CH:10]=[CH:9][CH:8]=2)[CH2:6][CH2:5][CH2:4][CH2:3][CH:2]=1>C(O)C.[Pd]>[CH:1]1([C:7]2[N:12]=[C:11]([C:13]([OH:15])=[O:14])[CH:10]=[CH:9][CH:8]=2)[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6]1

Participants

4

Reactant 1

HCID 710872336-Cyclohexenyl-pyridine-2-carboxylic acid

Product 1

HCID 681621566-Cyclohexyl-pyridine-2-carboxylic acid

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

To a solution of 6-cyclohexenyl-pyridine-2-carboxylic acid (0.8 g, 3.94 mmol) in ethanol (50 mL) was added 10% palladium on carbon (20%, 0.16 g) under an atmosphere of nitrogen. The suspension was degassed under vacuum and exchanged with hydrogen several times. The mixture was stirred under hydrogen balloon at ambient temperature overnight. The reaction mixture was filtered through a pad of celite, the pad was washed with ethanol and the combined filtrates were concentrated to dryness. The crude title compound (0.62 g, green oil) was used for the next reaction step without further purification; MS (EI): m/e 206.2 [M+H]+

Workup

  1. customThe suspension was degassed under vacuum
  2. filtrationThe reaction mixture was filtered through a pad of celite
  3. washthe pad was washed with ethanol
  4. concentrationthe combined filtrates were concentrated to dryness
  5. customThe crude title compound (0.62 g, green oil) was used for the next reaction step without further purification

Sources & evidence

ORD record
ord-c5b7db4d7b3649f38cba0c072bdf07f4
Source dataset
uspto-grants-2016_03
Patent number
US09290451B2

Reaction notes

Loading…